The purpose of this research was to examine the disconnect between urban school expectations and actual lived realities of marginalized students. Taking into consideration the conversation surrounding the definitions of urban education, and the importance of school connectedness with youth, we chose to focus on the lives of five former high students navigating their education. Our qualitative study found that the students' lives presented challenges to linear pathways to school success. Drawing from the student's stories, recommendations are proposed to disrupt the deficit definition of urban education and educational leaders initiate critical school connections to students lived realities.